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A4882

6-Thioguanine

Name: 6-Thioguanine
Brand: SIGMA

≥98%, Guanine antimetabolite, powder

Synonym(s):

2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol

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About This Item

Empirical Formula (Hill Notation):

C₅H₅N₅S

CAS Number:

154-42-7

Molecular Weight:

167.19

NACRES:

NA.77

PubChem Substance ID:

24890748

UNSPSC Code:

12352202

EC Number:

205-827-2

MDL number:

MFCD00233553

Beilstein/REAXYS Number:

157765

Assay:

≥98%

Biological source:

synthetic (organic)

Form:

powder

Solubility:

1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow

Storage temp.:

room temp

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Properties

Product Name

6-Thioguanine, ≥98%

biological source

synthetic (organic)

Quality Level

200

assay

≥98%

form

powder

mp

≥300 °C (lit.)

solubility

1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow

storage temp.

room temp

SMILES string

NC1=Nc2nc[nH]c2C(=S)N1

InChI

1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

InChI key

WYWHKKSPHMUBEB-UHFFFAOYSA-N

Gene Information

human ... IMPDH1(3614), IMPDH2(3615)

Description

General description

6-Thioguanine is a variant of guanine with hydrogen bonding at the N-7 of the purine ring. Its association with cytosine alters the dimension of the base stacking. 6-Thioguanine usage in treating inflammatory bowel disease (IBD) contributes to nodular regenerative hyperplasia (NRH) in the liver.

Application

6-Thioguanine has been used:

to induce autophagy and apoptosis in colorectal cancer cell lines HCT116
as a selection marker in the mutation and survival assay in chinese hamster lung fibroblasts culture V79
as a selection marker in clonogenic Lung metastasis assay of 4T1-luc cells

Biochem/physiol Actions

Antimetabolite used in the treatment of leukemias. Competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase, which catalzyes a critical step in the generation of purine nucleotides.

Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.

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pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c